Meaning of "Which Way Does That Old Pony Run" by Lyle Lovett

The lyrics of "Which Way Does That Old Pony Run" by Lyle Lovett explore the internal conflict of a man torn between two lives. The cowboy reminisces about his past as the best in the land, but acknowledges that he was settled down by a woman who changed his life. The question of which way his old pony runs becomes a metaphor for his longing to return to his roots, to the simple life of a cowboy. Despite the comforts and riches of his current life, he realizes that true wealth lies in the freedom and simplicity of his old way of life. The song captures the bittersweet struggle between love and independence, tradition and change, ultimately leaving the listener to ponder the choices we make in life and the longing for what we leave behind.